GB862269A - New azo dyestuffs - Google Patents
New azo dyestuffsInfo
- Publication number
- GB862269A GB862269A GB31143/57A GB3114357A GB862269A GB 862269 A GB862269 A GB 862269A GB 31143/57 A GB31143/57 A GB 31143/57A GB 3114357 A GB3114357 A GB 3114357A GB 862269 A GB862269 A GB 862269A
- Authority
- GB
- United Kingdom
- Prior art keywords
- beta
- amide
- acid
- chloroethyl
- dyestuffs
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 abstract 5
- 239000000460 chlorine Substances 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- 239000000463 material Substances 0.000 abstract 5
- 239000004753 textile Substances 0.000 abstract 5
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- 230000008878 coupling Effects 0.000 abstract 4
- 238000010168 coupling process Methods 0.000 abstract 4
- 238000005859 coupling reaction Methods 0.000 abstract 4
- 239000004952 Polyamide Substances 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 239000006185 dispersion Substances 0.000 abstract 3
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 3
- 229920002647 polyamide Polymers 0.000 abstract 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- REXYIKXSNOVYSZ-UHFFFAOYSA-N 1-(2-aminophenoxy)propan-2-one Chemical compound CC(=O)COC1=CC=CC=C1N REXYIKXSNOVYSZ-UHFFFAOYSA-N 0.000 abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 abstract 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- -1 azo compound Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Chemical group 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 239000000835 fiber Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 abstract 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 abstract 1
- KXEMVGQZZLRLBE-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1S(Cl)(=O)=O KXEMVGQZZLRLBE-UHFFFAOYSA-N 0.000 abstract 1
- ZSKNGCRQEDFRNJ-UHFFFAOYSA-N 2-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC=CC=C1C(Cl)=O ZSKNGCRQEDFRNJ-UHFFFAOYSA-N 0.000 abstract 1
- AWEHSEOYWOMMFS-UHFFFAOYSA-N 6-acetamidonaphthalene-2-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=CC2=CC(NC(=O)C)=CC=C21 AWEHSEOYWOMMFS-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 229950011260 betanaphthol Drugs 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 125000006421 chlorocycloalkyl group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- NQRLPDFELNCFHW-UHFFFAOYSA-N nitroacetanilide Chemical compound CC(=O)NC1=CC=C([N+]([O-])=O)C=C1 NQRLPDFELNCFHW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 abstract 1
- YERLJJDMKZJPBL-UHFFFAOYSA-M sodium;3-(diethylamino)benzenesulfonate Chemical compound [Na+].CCN(CC)C1=CC=CC(S([O-])(=O)=O)=C1 YERLJJDMKZJPBL-UHFFFAOYSA-M 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/523—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl amido or hydroxyalkyl amino sulfonyl group, a quaternised or non-quaternised amino alkyl sulfonyl amido group, or a substituted alkyl amino sulfonyl group, or a halogen alkyl sulfonyl amido or halogen alkyl amino sulfonyl group or a vinyl sulfonylamido or a substituted vinyl sulfonamido group
- C09B62/527—Azo dyes
- C09B62/53—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B39/00—Other azo dyes prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
- C09B62/66—Azo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
Abstract
2 - Anisidine - 4 - N - (beta - chloroethyl) amide, 2 - amino - 5 - nitrobenzenesulphon - N - (betachloroethyl) amide and 2-naphthylamine-6-sulphon - N - (beta - chloroethyl) amide are made by reacting beta-chloroethylamine with p acetyl-2-anisidine-4-sulphochloride (prepared by heating acetyl-2-anisidine with chlorosulphonic acid), acetyl-2-anisidine with chlorosulphonic acid), 4 - nitroacetanilide - 2 - sulphonyl chloride (prepared by reacting 4-nitroacetanilide-2-sulphonic acid with a mixture of phosphorus oxychloride and phosphorus pentachloride) and 2-acetylaminonaphthalene-6-sulphonyl chloride respectively and hydrolysing the acetylated amino groups with hydrochloric acid. 3 - N:N - Diethylaminobenzenesulphon - N - (beta - chloroethyl) amide and 3 - (21 - chloroethyl) aminosulphonylbenzoylchloride are made by reacting beta-chloroethylamine with 3-N:N-diethylaminobenzenesulphonyl chloride (prepared by treating sodium diethyl metanilate with chlorsulphonic acid) and benzoic acid-3-sulphonyl chloride respectively. 2 - Naphthol - 6 - sulphon - N - (beta - chloroethyl) amide is made by reacting beta-chloroethylamine with 2-hydroxy-1-naphthoic acid 6-sulphonyl chloride and decarboxylating the amide formed with hydrochloric acid. 3 - Acetoacetylaminobenzenesulphon - N - beta-chloroethyl) amide is made by reacting diketene with 3-aminobenzene sulphon-N-(betachlorethyl) amide. 2 - Amino - 4 - trifluoromethylbenzenesulphonN-(beta-chloroethyl) amide is made by reacting 2 - nitro - 4 - trifluoromethylchlorobenzene with sodium disulphide, passing chlorine into the 2:21 - dinitro - 4:41 - di - (trifluoromethyl) diphenyldisulphide so obtained to give 2-nitro-4-trifluoromethylbenzenesulphonyl chloride and reacting the latter with beta-chloroethylamine to obtain 2-nitro-4-trifluoromethylbenzene-sulphon-N-(beta-chloroethyl) amide which is then reduced.ALSO:The invention comprises water-insoluble azo dyestuffs which are free from sulphonic acid, carboxylic acid and acylsulphonamide groups and which contain not more than one phenolic hydroxyl or enolizable carbonyl group and at least one group of the formula -SO2NRR1, each of which is directly attached to a different aryl nucleus present in the azo dyestuff, wherein R represents a chloro- or bromo-alkyl or chloroor bromo-cycloalkyl radical, R1 is hydrogen or a substituted or unsubstituted hydrocarbon radical or a chloro- or bromo-alkyl or chloro- or bromo-cycloalkyl radical or R and R1 are joined to form with the nitrogen atom a heterocyclic ring containing a chlorine or bromine atom. The dyestuffs are made by diazotization and coupling or by converting the appropriate azo compound containing one or more sulphonic acid groups to the sulphonyl chloride and treating the latter with an amine of the formula HNRR1. Lists of aromatic amines, coupling components and azo compounds which may be used are given. The dyestuffs of the invention include those of the formulae:- <FORM:0862269/IV(c)/1> where B is a substituted or unsubstituted benzene or naphthalene nucleus, D is a substituted or unsubstituted amino group, X is a hydrogen or halogen atom and Y is chlorine or bromine, <FORM:0862269/IV(c)/2> where P is a substituted or unsubstituted aryl or heterocyclic nucleus, Y is chlorine or bromine and Z and Z1 are substituted or unsubstituted alkyl radicals and may be the same or different, and <FORM:0862269/IV(c)/3> and <FORM:0862269/IV(c)/4> where Y is a chlorine or bromine atom and the benzene rings may be substituted. Many examples are given. The dyestuffs colour animal fibres such as wool, silk and regenerated protein fibres and artificial fibres such as cellulose ester fibres, polyamide, polyurethane, polyester, polyacrylonitrile and modified polyacrylonitrile fibres from aqueous dispersions by known methods. The dyestuffs may be used singly or in mixtures and may be applied to artificial textile materials in conjunction with a prior, simultaneous or subsequent treatment with an amine, phenol or thiophenol. The dyestuffs may be formed on the textile material by treating the latter separately or simultaneously with aqueous solutions or dispersions of appropriate coupling components and of aromatic or heterocyclic amines in conjunction with nitrous acid. The dyestuffs may also be applied to textile materials in the form of printing pastes containing the usual thickeners and adjuvants. In Examples (1) polyamide textile material, (92) silk and (93) modified polyacrylonitrile fibre are dyed with an aqueous dispersion of dyestuff followed by an alkaline treatment; and (94) a polyamide textile material and (95) a cellulose acetate rayon fibre are dyed by treatment with an amine and nitrous acid followed by a coupling component. Specification 548,903 is referred to.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31143/57A GB862269A (en) | 1957-10-04 | 1957-10-04 | New azo dyestuffs |
| CH6466058A CH400411A (en) | 1957-10-04 | 1958-10-03 | Process for the production of new azo dyes |
| US335661A US3314935A (en) | 1957-10-04 | 1964-01-03 | Monoazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31143/57A GB862269A (en) | 1957-10-04 | 1957-10-04 | New azo dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB862269A true GB862269A (en) | 1961-03-08 |
Family
ID=10318662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31143/57A Expired GB862269A (en) | 1957-10-04 | 1957-10-04 | New azo dyestuffs |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3314935A (en) |
| CH (1) | CH400411A (en) |
| GB (1) | GB862269A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4111930A (en) * | 1969-07-17 | 1978-09-05 | Sandoz Ltd. | Monoazo dyes having an aryloxyalkyl group on the nitrogen atom in the para position of a 1,4-phenylene coupling component radical |
| DE2004442A1 (en) * | 1970-01-31 | 1971-08-05 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Monoazo dyes |
| CA925859A (en) * | 1970-01-31 | 1973-05-08 | Siegel Edgar | Monoazo dyestuffs |
| US3869442A (en) * | 1971-10-29 | 1975-03-04 | Eastman Kodak Co | Phenyl-azo-n-acylamidoethylaniline compounds |
| GB2031927A (en) * | 1978-09-08 | 1980-04-30 | Ici Ltd | Dyestuffs |
| JP2772724B2 (en) * | 1990-07-25 | 1998-07-09 | 富士写真フイルム株式会社 | Photographic processing composition and processing method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE664258C (en) * | 1931-09-20 | 1938-08-24 | Siemens Schuckertwerke Akt Ges | Safety device for several conveyor motors fed from the same network and working simultaneously |
| US2766231A (en) * | 1953-01-28 | 1956-10-09 | Ciba Ltd | Monoazo-dyestuffs |
| US3154533A (en) * | 1957-12-18 | 1964-10-27 | Basf Ag | New azo dyestuffs |
| US3050516A (en) * | 1958-02-07 | 1962-08-21 | Sandoz Ag | Monoazo dyestuffs of low solubility in water |
-
1957
- 1957-10-04 GB GB31143/57A patent/GB862269A/en not_active Expired
-
1958
- 1958-10-03 CH CH6466058A patent/CH400411A/en unknown
-
1964
- 1964-01-03 US US335661A patent/US3314935A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH400411A (en) | 1965-10-15 |
| US3314935A (en) | 1967-04-18 |
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